


Cupid's Wayward Arrow - Valentine's Day

by TheOriginalSinner888



Series: Holdiay Sins [5]
Category: Original Work
Genre: Classroom Sex, Cupid's Arrow, Desk Sex, Drug-Induced Sex, Dubious Consent, Extremely Dubious Consent, F/M, Greek Mythology - Freeform, Older Man/Younger Woman, Rape/Non-con Elements, Rough Sex, Semi-Public Sex, Sex, Teacher-Student Relationship, Underage Sex, Vaginal Sex, Wall Sex
Language: English
Status: Completed
Published: 2020-02-18
Updated: 2020-02-18
Packaged: 2021-02-27 23:27:54
Rating: Explicit
Warnings: Rape/Non-Con, Underage
Chapters: 1
Words: 1,787
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/22784065
Author URL: https://archiveofourown.org/users/TheOriginalSinner888/pseuds/TheOriginalSinner888
Summary: Cupid picked a special case every year on Valentine's day to show someone the way to true love.  His arrow was true and he never missed.  Except for this year...
Relationships: Original Female Character/Original Male Character
Series: Holdiay Sins [5]
Series URL: https://archiveofourown.org/series/1531733
Comments: 7
Kudos: 429





	Cupid's Wayward Arrow - Valentine's Day

**Author's Note:**

> Sorry this is late! Happy Valentine's Day!

Being Cupid, son of Aphrodite, was mostly about basking in the love of his wife, Psyche. But on Valentine’s Day – his day, he took to the mortal world to spread love to others. To show them true love – the kind of love he had – and help them find their happily ever after.

That was his job. 

He’d float down to the mortal – unseen by their eyes – and strike them with his arrow. Whoever he hit first, would fall in love with the person he hit second. And his arrow never missed.

But there was a first time for everything.

He always found himself a special case, client, what-have-you. This year, he had been focused on finding Mr. Jason Wright, his true love. Especially after poor Mr. Wright had gone through a tormenting divorce with his first wife who just used him for stability. He had been forced to downgrade to a small apartment that he could afford on his teachers’ salary. A sad sap – he’d become. But Cupid was out to change that.

There was a new-ish teacher at his school, Miss Penelope Sanchez, had arrived at the school and Cupid had determined that she was a perfect love match for Mr. Wright. But Jason was gun-shy. So, Cupid would have to give him a little push.

He floated down to the mortal world, down to Oregon, down to a small city called Qualene, down to a modest sized school called Qualene River High School. He floated through the halls, to Jason Wright’s US History class. He observed Jason teaching his class of Juniors about the civil war. He was energetic about the subject, passionate. But certainly, had an air of loneliness about him.

Cupid knew he could fix that. So, with a steady hold on his bow and excellent aim, he struck Jason in the back with his heart-shaped arrow. Now, he needed to find Penelope.

The shrill bell rang, and he was floating in masses of teachers and students in the hallways. He noticed Miss Penelope Sanchez shyly glancing over at the history classroom as she let her own students out of class to head to the next one before lunch. Cupid took up his bow and aimed for Penelope – right at her heart. He had impeccable aim. But almost impeccably poor timing in that moment.

Because as his fingers release the arrow from his bow and sent it flying through the air for Penelope, a student stepped in front of her, chatting. Before Cupid could utter a word or move, the arrow struck that girl in the back of her shoulder.

He was horrified. This had never happened to him before. What could he possibly do?

The girl was young. Sixteen or seventeen. Shoulder length sandy blonde hair, dark eyes, cupid bow shaped pink lips. She was pretty – but that didn’t make her appropriate for Jason Wright.

He could feel himself sweating nervously as the girl made her way to US History with Mr. Wright. Even more so as Jason’s hungry eyes took in her form with heart shaped pupils dilating.

He hovered, unseen, at the door as class began. There was a definite extra pep in his step as Jason taught this class. He smiled wider and spoke with open enthusiasm. But his eyes rarely strayed from the sandy blonde girl. It was obvious. Even she noticed it.

Cupid started muttering curses to himself as class went on.

When the bell rang again and the students started dispersing to lunch, Mr. Wright called out, “Um, Anna, can you hang back a minute? I’d like to discuss something with you.”

Anna – the sandy blonde – got some looks from her classmates as she nervously hovered by the teacher’s desk until it was just the two of them.

“Thank you for staying, Anna,” Jason said brightly as he went to his door and locked it. “This is important.”

“Is it about my test, Mr. Wright?” Anna asked curiously.

“No, not at all. You’re doing wonderfully,” Jason complimented ardently. “What I want to talk to you about – is us, Anna.”

Anna pursed her lips in confusion. “What are you talking about, Mr. Wright?”

“You know what I’m talking about,” he insisted in a hushed voice. He stalked up to her until he was right in front of her. Cupid could only watch – unseen and unheard – as his mistake played out right in front of him. Jason took a deep breath before speaking lowly and whispering to her, “We can’t fight this.”

“Mr. Wright—”

Anna was cut off by the lips of her teachers on hers. She let out a squeak and squirmed, but Jason wrapped his arms around her and pulled her close. She was half crushed into the edge of his desk as he devoured her mouth passionately and already reached with one free hand to cup her petite breasts and pluck at her small nipples beneath her thin top.

She yelped again and tried to lurch back, but she was pinned between his hard body and the desk. Jason’s hand left her breasts and started trailing down her flat stomach until he teased the button of her jean shorts. He deftly undid it as well as her zipper. And then his hand was slipping into her shorts and teasing her slit through her cotton panties.

Her yelp went up several octaves and she was breathing harshly when Jason released her mouth to plant a series of kisses along her neck and chest. Anna couldn’t seem to breathe or speak. She did try to tilt away from Jason’s touch. But even Cupid could see that her efforts to escape were growing weary. She was growing aroused by his touch.

Jason grinned against her neck. “I’m making you wet, Anna? That right?”

“Ngh,” she whimpered.

Jason roughly grabbed her hand and pressed her palm against his hard cock inside his trousers. “Feel that, baby? That’s for you. Can’t wait to get inside you.”

Anna’s eyes widened but she still couldn’t speak as Jason shoved her shorts down around her ankles.

“Kick those off,” he groaned at her as his hand unabashedly stroked her moist cunt through her pink panties. She did as told, shaking a little. He pressed his finger hard against the little bundle of nerves hiding behind the pink cotton and made wide circles.

Anna’s legs sporadically shook and then went limp as he knees buckled. Jason was quick to catch her and perch her perky butt on the edge of his desk, her legs left to dangle. He chuckled and kissed her.

“Don’t worry. I’ll be gentle,” he cooed to her. He undid his trousers and reached in to fish out his throbbing dick. He guided Anna’s hand back to his erection and wrapped her fingers around him. “Go on, baby. Touch me.”

Unpracticed, she obeyed and haphazardly started stroking her hand up and down his length. He groaned as he pressed sloppy kissed to her neck and his hand dived into her panties. His hand touched her without barrier. He felt her wetness and heat unimpeded. He stroked her pussy and started toying with her clit again until Anna finally let out a moan.

Jason grinned and chuckled darkly. He then suddenly pushed two fingers into her cunt and started fucking her with his fingers.

Anna yelped in surprise and a hint of pain and reared back. But he leaned over her and held her hand to his dick as he kissed her. His fingers moved quickly. He enjoyed the sounds of her pussy sucking them in. He plunged his tongue into her mouth and explored. She tasted so sweet. She was perfect.

He bent his fingers inside her and explored until he found that spot that made her keen against her will. “Mmm, there it is. Come on, baby. Cum for me, hmm?”

Anna couldn’t control her body or her reaction as she suddenly seized up and whined, cumming hard on his hand. 

And without much ceremony or thought, Jason pushed his trousers down to his knees, pressed the bulbous mushroom head of his cock against her fluttering pussy, and pushed right through.

“AH!” Anna screamed in more pain than shock. “You’re too big, you have to get out!”

Jason shook his head. “Can’t do that.” He groaned as he pressed his hips flushed with hers. “You feel too good. It’ll get better, baby. Trust me.”

“No,” Anna whimpered as he slid his cock out of her – only halfway – and then plunged right back in.

Jason settled into a rhythm, with his chest pressed against hers and hands encased her hips. And began rutting into her like he was in a trance. Anna – having almost fallen against Jason’s computer – wrapped her arms around his neck to keep herself secure. Her face was screwed up in discomfort as her cunt took his hard cock repeatedly.

Jason grunted as he spread Anna’s legs apart wider and coached her to wrap them around his hips. He pressed his palms into her ass cheeks and held her up over the desk. He supported her petite form and basically dropped her pussy on his cock. Cupid listened to the slapping of their skin.

Anna keened again out of nowhere as her pussy clenched onto him as she came hard. “Ugh!”

“Fuck yeah, Anna,” Jason grunted. He weaved his fingers into her hair and gripped tight as he fucked her little body. “I love the feeling of you cumming on my cock!”

Anna was little more than a limp rag doll in his arms. He spun them around and pressed her back against the wall next to his board. He hooked his elbows under her knees and kept her spread wide for his invading dock. Her head fell back, eyes closed – biting into her lower lip.

Jason nibbled and licked her neck and what he could crane to reach of her chest. He pistoned into her like a machine. “I need you to cum for me again, baby doll. Think you can do that for me? I’m getting close to cumming for you.”

Anna’s eyed widened again as her brain caught up with her words. But her third orgasm was already beginning to assault her, and she couldn’t form words as she came on his cock again. “Ngh, ah, ah, oh!”

The way her pussy squeezed him, set Jason off like a fire hydrant. He lurched inside her and started spilling his cum into her body. He grunted harshly into her neck and kept flush with her as her cunt milked all of his cum out of his body.

Jason panted as he pressed deliriously happy kisses all over Anna’s face and whispered, “Happy Valentine’s day, my love.”


End file.
